ChemSpider 2D Image | SF8282645 | C19H20O3

SF8282645

  • Molecular FormulaC19H20O3
  • Average mass296.360 Da
  • Monoisotopic mass296.141235 Da
  • ChemSpider ID140851

  • defined stereocentres - 1 of 1 defined stereocentres

More details:

Featured data source
Natural Product Updates

Validated by Experts, Validated by Users, Non-Validated, Removed by Users

(1R)-1,6,6-Trimethyl-1,2,6,7,8,9-hexahydrophenanthro[1,2-b]furan-10,11-dion [German] [ACD/IUPAC Name]
(1R)-1,6,6-Trimethyl-1,2,6,7,8,9-hexahydrophenanthro[1,2-b]furan-10,11-dione [ACD/IUPAC Name]
(1R)-1,6,6-Triméthyl-1,2,6,7,8,9-hexahydrophénanthro[1,2-b]furane-10,11-dione [French] [ACD/IUPAC Name]
(R)-(-)-1,6,6-Trimethyl-1,2,6,7,8,9-hexahydrophenanthro[1,2-b]furan-10,11-dione
1,2,6,7,8,9-hexahydro-1,6,6-trimethyl- (R)-phenanthro(1,2-b)furan-10,11-dione
35825-57-1 [RN]
Cryptotanshinon
Cryptotanshinone
MFCD07636810
Phenanthro(1,2-b)furan-10,11-dione, 1,2,6,7,8,9-hexahydro-1,6,6-trimethyl-, (R)-
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Validated by Experts, Validated by Users, Non-Validated, Removed by Users

5445400 [DBID]
5E9SXT166N [DBID]
NCI60_031208 [DBID]
NSC686518 [DBID]
UNII:5E9SXT166N [DBID]
ZINC02109876 [DBID]
  • References
  • Experimental Physico-chemical Properties
  • Miscellaneous

    • Target Organs:

      STAT inhibitor TargetMol T2814

    • Bio Activity:

      Biochemicals & small molecules/Antagonists & inhibitors Hello Bio [HB1434]
      Cell Biology Tocris Bioscience 3713
      Cryptotanshinone(Tanshinone c) is a potent STAT3 inhibitor(IC50 =4.6 uM); inhibited STAT3 Tyr705 phosphorylation in DU145 prostate cancer cells. MedChem Express
      Cryptotanshinone(Tanshinone c) is a potent STAT3 inhibitor(IC50 =4.6 uM); inhibited STAT3 Tyr705 phosphorylation in DU145 prostate cancer cells.;IC50 value: 4.6 uM [1];Target: STAT3;In vitro: Cryptotanshinone rapidly inhibited STAT3 Tyr705 phosphorylation in DU145 prostate cancer cells and the growth of the cells through 96 hours of the treatment. Inhibition of STAT3 Tyr705 phosphorylation in DU145 cells decreased the expression of STAT3 downstream target proteins such as cyclin D1, survivin, and Bcl-xL.Although phosphorylation of Janus-activated kinase (JAK) 2 was inhibited by 7 micromol/L cryptotanshinone at 24 hours, inhibition of STAT3 Tyr705 phosphorylation occurred within 30 minutes and the activity of the other proteins was not affected [1]. Cotreatment with imatinib and CPT showed a significant synergistic killing effect in both imatinib sensitive and resistant CML cell lines, as well as primary CML cells [3].;In vivo: Cryptotanshinone significantly reduced ovulation rates MedChem Express HY-N0174
      Cytokine and NF-kB Signaling Tocris Bioscience 3713
      JAK/STAT Signaling TargetMol T2814
      JAK/STAT Signaling; MedChem Express HY-N0174
      Major tanshinone isolated from Salvia miltiorrhiza that exhibits multiple activities. Exhibits antitumor activity via inhibition STAT3 activity (IC50 = 4.6 ?M). Displays antibacterial and anti-inflamm atory activity and acts as an antidiabetes and antiobesity agent via activation of AMP-activated protein kinase (AMPK). Also improves cognitive impairment in Alzheimer's disease transgenic mice by inh ibition of acetylcholinesterase (IC50 = 4.09 ?M) and reduction in A? peptide generation. Tocris Bioscience 3713
      Major tanshinone isolated from Salvia miltiorrhiza that exhibits multiple activities. Exhibits antitumor activity via inhibition STAT3 activity (IC50 = 4.6 ?M). Displays antibacterial and anti-inflammatory activity and acts as an antidiabetes and antiobesity agent via activation of AMP-activated protein kinase (AMPK). Also improves cognitive impairment in Alzheimer's disease transgenic mice by inhibition of acetylcholinesterase (IC50 = 4.09 ?M) and reduction in A? peptide generation. Tocris Bioscience 3713
      Major tanshinone isolated from Salvia miltiorrhiza that exhibits multiple activities. Exhibits antitumor activity via inhibition STAT3 activity (IC50 = 4.6 muM). Displays antibacterial and anti-inflammatory activity and acts as an antidiabetes and antiobesity agent via activation of AMP-activated protein kinase (AMPK). Also improves cognitive impairment in Alzheimer's disease transgenic mice by inhibition of acetylcholinesterase (IC50 = 4.09 muM) and reduction in Abeta peptide generation. Tocris Bioscience 3713
      Proteins - Other/STAT Hello Bio [HB1434]
      Signal Transduction Tocris Bioscience 3713
      STAT Tocris Bioscience 3713
      STAT MedChem Express HY-N0174
      STAT3 TargetMol T2814
      STAT3 inhibitor Hello Bio [HB1434]
      STAT3 inhibitor (IC<sub>50</sub> = 4.6 &micro;M). Also inhibits human acetylcholinesterase (AChE), butyrylcholinesterase (BuChE) and SHP2 (IC<sub>50</sub> values are 4.09, 6.38 and 22.5 &micro;M respectively). Shows anti-Alzheimer's disease, anticancer, antidiabetic and antiobesity actions. Hello Bio [HB1434]
      STAT3 inhibitor. Also displays multiple other activities Tocris Bioscience 3713

Predicted data is generated using the ACD/Labs Percepta Platform - PhysChem Module, version: 14.00

Density: 1.2±0.1 g/cm3
Boiling Point: 459.0±45.0 °C at 760 mmHg
Vapour Pressure: 0.0±1.1 mmHg at 25°C
Enthalpy of Vaporization: 71.9±3.0 kJ/mol
Flash Point: 203.4±28.8 °C
Index of Refraction: 1.603
Molar Refractivity: 82.2±0.4 cm3
#H bond acceptors: 3
#H bond donors: 0
#Freely Rotating Bonds: 0
#Rule of 5 Violations: 0
ACD/LogP: 4.93
ACD/LogD (pH 5.5): 4.14
ACD/BCF (pH 5.5): 824.51
ACD/KOC (pH 5.5): 4256.13
ACD/LogD (pH 7.4): 4.14
ACD/BCF (pH 7.4): 824.51
ACD/KOC (pH 7.4): 4256.13
Polar Surface Area: 43 Å2
Polarizability: 32.6±0.5 10-24cm3
Surface Tension: 49.7±5.0 dyne/cm
Molar Volume: 239.5±5.0 cm3

Predicted data is generated using the US Environmental Protection Agency�s EPISuite™ 

                        
 Log Octanol-Water Partition Coef (SRC):
    Log Kow (KOWWIN v1.67 estimate) =  4.75

 Boiling Pt, Melting Pt, Vapor Pressure Estimations (MPBPWIN v1.42):
    Boiling Pt (deg C):  422.35  (Adapted Stein & Brown method)
    Melting Pt (deg C):  176.33  (Mean or Weighted MP)
    VP(mm Hg,25 deg C):  6.36E-008  (Modified Grain method)
    Subcooled liquid VP: 2.37E-006 mm Hg (25 deg C, Mod-Grain method)

 Water Solubility Estimate from Log Kow (WSKOW v1.41):
    Water Solubility at 25 deg C (mg/L):  1.139
       log Kow used: 4.75 (estimated)
       no-melting pt equation used

 Water Sol Estimate from Fragments:
    Wat Sol (v1.01 est) =  1.3155 mg/L

 ECOSAR Class Program (ECOSAR v0.99h):
    Class(es) found:
       Vinyl/Allyl Ethers

 Henrys Law Constant (25 deg C) [HENRYWIN v3.10]:
   Bond Method :   5.95E-010  atm-m3/mole
   Group Method:   Incomplete
 Henrys LC [VP/WSol estimate using EPI values]:  2.177E-008 atm-m3/mole

 Log Octanol-Air Partition Coefficient (25 deg C) [KOAWIN v1.10]:
  Log Kow used:  4.75  (KowWin est)
  Log Kaw used:  -7.614  (HenryWin est)
      Log Koa (KOAWIN v1.10 estimate):  12.364
      Log Koa (experimental database):  None

 Probability of Rapid Biodegradation (BIOWIN v4.10):
   Biowin1 (Linear Model)         :   0.1298
   Biowin2 (Non-Linear Model)     :   0.0031
 Expert Survey Biodegradation Results:
   Biowin3 (Ultimate Survey Model):   2.2486  (months      )
   Biowin4 (Primary Survey Model) :   3.1884  (weeks       )
 MITI Biodegradation Probability:
   Biowin5 (MITI Linear Model)    :  -0.0669
   Biowin6 (MITI Non-Linear Model):   0.0068
 Anaerobic Biodegradation Probability:
   Biowin7 (Anaerobic Linear Model): -0.6274
 Ready Biodegradability Prediction:   NO

Hydrocarbon Biodegradation (BioHCwin v1.01):
    Structure incompatible with current estimation method!

 Sorption to aerosols (25 Dec C)[AEROWIN v1.00]:
  Vapor pressure (liquid/subcooled):  0.000316 Pa (2.37E-006 mm Hg)
  Log Koa (Koawin est  ): 12.364
   Kp (particle/gas partition coef. (m3/ug)):
       Mackay model           :  0.00949 
       Octanol/air (Koa) model:  0.568 
   Fraction sorbed to airborne particulates (phi):
       Junge-Pankow model     :  0.255 
       Mackay model           :  0.432 
       Octanol/air (Koa) model:  0.978 

 Atmospheric Oxidation (25 deg C) [AopWin v1.92]:
   Hydroxyl Radicals Reaction:
      OVERALL OH Rate Constant =  63.3716 E-12 cm3/molecule-sec
      Half-Life =     0.169 Days (12-hr day; 1.5E6 OH/cm3)
      Half-Life =     2.025 Hrs
   Ozone Reaction:
      OVERALL Ozone Rate Constant =   125.999992 E-17 cm3/molecule-sec
      Half-Life =     0.009 Days (at 7E11 mol/cm3)
      Half-Life =     13.097 Min
   Fraction sorbed to airborne particulates (phi): 0.344 (Junge,Mackay)
    Note: the sorbed fraction may be resistant to atmospheric oxidation

 Soil Adsorption Coefficient (PCKOCWIN v1.66):
      Koc    :  208.9
      Log Koc:  2.320 

 Aqueous Base/Acid-Catalyzed Hydrolysis (25 deg C) [HYDROWIN v1.67]:
    Rate constants can NOT be estimated for this structure!

 Bioaccumulation Estimates from Log Kow (BCFWIN v2.17):
   Log BCF from regression-based method = 2.955 (BCF = 901.6)
       log Kow used: 4.75 (estimated)

 Volatilization from Water:
    Henry LC:  5.95E-010 atm-m3/mole  (estimated by Bond SAR Method)
    Half-Life from Model River: 1.694E+006  hours   (7.058E+004 days)
    Half-Life from Model Lake : 1.848E+007  hours   (7.7E+005 days)

 Removal In Wastewater Treatment:
    Total removal:              68.23  percent
    Total biodegradation:        0.61  percent
    Total sludge adsorption:    67.62  percent
    Total to Air:                0.00  percent
      (using 10000 hr Bio P,A,S)

 Level III Fugacity Model:
           Mass Amount    Half-Life    Emissions
            (percent)        (hr)       (kg/hr)
   Air       0.00211         0.207        1000       
   Water     8.52            1.44e+003    1000       
   Soil      76.6            2.88e+003    1000       
   Sediment  14.9            1.3e+004     0          
     Persistence Time: 2.55e+003 hr

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